Jason's Date
by MTWKing
Summary: After years of failure, Jason finally gets a date, while he and the gang are in the Hoenn Region. Despite his protests, Rachel convinces Tanner to help her spy on Jason and his date, Caroline. What kind of trouble could they get themselves into? Memories of Past Travels One-Shot


**What's up Internet? I'm back with another story set in my "Memories of Past Travels" Universe. Be sure to check that story and my others** **out (and my Bio too** ) **if you want to learn more about the characters involved in this one (Not necessary). This one takes place during Tanner, Rachel and Jason's journey through Hoenn. Without further ado, let's get to the story.**

 **Summary: After years of failure, Jason finally gets a date, while he and the gang are in the Hoenn Region. Despite his protests, Rachel convinces Tanner to help her spy on Jason and his date, Caroline. What kind of trouble could they get themselves into?**

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Jason's Date

Tanner Riverton thought he'd seen it all. Team Rocket's attempt at world domination, twice, both the Indigo and Johto leagues, Mewtwo, Lugia, Ho-oh among other legendary Pokémon. But not in a million years did he think he would see his oldest travelling companion about to head off on a date.

As he sat on his bed with his Umbreon lying next to him, Tanner watched Jason run around their shared room in the Lilycove City Pokémon centre. After years of seeing his mentor get rejected, Tanner finally saw a girl say yes.

"How do I look?" Jason asked as he turned to face the aspiring 12-year-old Pokémon trainer.

Jason was wearing a white button up shirt and a pair of dressier looking black pants. His normal travelling shoes were replaced by dress shoes. Jason's brown hair was slicked back and neatly combed. The fifteen-year-old's grey eyes gave away his nervousness about his date.

"Aren't you over doing it a little bit?" Tanner responded as he took off his red baseball cap and placed it on his night stand. "I mean, do you really think you need to dress up for this?"

"Of course, I do!" Jason said frantically as he looked in the mirror. "I need to show Caroline how classy I am, I need to show her that I clean up well."

Tanner rolled his brown eyes at Jason's comment.

"Umbre!" Umbreon exclaimed as she listened to the conversation between her trainer and his friend.

"Umbreon's right, are you really that classy?" Tanner asked. "You shouldn't have to try to impress Caroline anymore than you already have, she did say yes"

Jason started to calm down as he grabbed his wallet from his bag.

"You're right. I'm fine the way I am." He said. "When did you become so mature?"

"When did girls start taking an interest in you?"

"Ha ha ha…" Jason rolled his eyes. "Well I'm off to meet Caroline. Umbreon, make sure Tanner doesn't get into trouble"

"Umbreon!" Umbreon cried in affirmative.

"Hey!" Tanner rebutted as Jason left the room. The moonlight Pokémon stuck her tongue at her trainer, which Tanner chose to ignore.

"Who would of thought, Jason going out on a date" Tanner mused as he grabbed a map of the Hoenn Region out of his bag. He started to take notes of the different routes their group could travel to their next destination.

"So, if we travel to-" Tanner was cut off by someone knocking on the door.

"Come in!" As soon as Tanner spoke, the door swung open and his other traveling companion, Rachel rushed in. She scanned the room with her green eyes before she spoke.

"Did Jason leave for his date?"

"Yeah, you just missed him" Tanner replied as he looked back at his map.

Rachel tucked a strand of her chestnut colored hair behind her ear. She sat down on the end of Tanner's bed and reached to pat Umbreon who was lying next to Tanner's legs.

"I can't believe Jason finally got a date" Rachel said as she shook her head.

"That's the seventh time you've said that today" Tanner commented, seemingly not paying too much attention to the conversation.

"I mean, for years we've watched him try to get with any girl that so much as smiled at him" Rachel rambled on. "He'd usually get called a creep or get slapped but then he met Caroline. Then, they actually became friends and when he asked her out she said yes. Is there something wrong with her?"

Tanner put down his map and looked at Rachel who was still soothingly petting his Umbreon.

"They do have a lot of the same interests. They both love breeding Pokémon"

"But still, its Jason! Girls find him repulsive!" Rachel urged.

"Okay, what's the point Rach, I doubt you came over here just to talk about Jason's date" Tanner said. "Do you want to try and teach one of my Pokémon a weird new move again? Because last time, Lairon was-"

Tanner was interrupted by Rachel.

"I'm just worried about what might happen."

Tanner looked at Rachel inquisitively. She had a worried look on his face.

"What do you mean?" He asked. "Are you worried that Jason's date might go badly?"

"No, no" Rachel sighed as she looked away. "I'm worried about what might happen if Jason's date goes well"

Tanner was confused. Why would Rachel be worried about Jason's date going well? Wouldn't that be a good thing?

"Why are you worried about that?" Tanner questioned apprehensively. Despite him and Rachel being the same age, close friends and travel companions for 3 years now, Tanner didn't always understand what she was thinking. But this time, he had no clue why she was thinking the way she was.

"Because if this date goes well, Jason and Caroline could become a thing!" Rachel exclaimed. "If they start dating, Jason might leave us to travel with her. What would we do without Jason!? He cooks when we camp out! Or worse, Caroline could start traveling with us!"

"Woah, woah, woah, slow down!" Tanner stopped Rachel from rambling even further. "If Jason were to even want to travel with someone else, or head home for what ever reason, we would have to respect his decision. He's done so much for us that the least we could do would be to be happy and supportive for him."

Tanner paused to sit up and put his map away.

"And why would you be worried about Caroline travelling with us?"

Rachel sighed before she turned back to face Tanner.

"This may sound silly, but I'm worried that adding someone to our group might damage it."

"Damage it?" Tanner repeated.

"Yeah, damage it" Rachel said. "You, me and Jason have a great group dynamic, we're the best of friends and joke around a lot. I'm worried that some of what we do might change if Jason we're to bring a new girlfriend along"

"You shouldn't worry about that" Tanner smiled as he placed a hand on Rachel's shoulder comfortingly. "I'm sure if Jason were to ever get a girlfriend we would get along with her. But, how likely is it that Jason of all people is gonna get a girlfriend. Sure, Caroline's going on a date with him, but its Jason"

"Yeah," Rachel laughed at Tanner's joke. "I guess you're right. Thank you for that, I'm feeling a little better now"

"Good" Tanner smiled as he leaned back on to his bed.

Rachel suddenly had a mischievous idea as she suddenly jumped off the bed. She reached over and grabbed Tanner's wrist.

"Come on!" She said as she pulled Tanner off the bed. Umbreon jumped off the bed at Tanner's sudden movement.

"What are you doing?!" Tanner asked as stumbled to get his footing once Rachel let go of his wirst.

"We're going to spy on Jason's date!" Rachel exclaimed as she ran out of the room. "Hurry up slowpoke!"

Tanner grabbed his red hat off the nightstand and put it on his head. The young aspiring grabbed his backpack and slung it over his shoulder.

"I guess we should make sure she stays out of trouble, eh?" Tanner said as he looked to Umbreon.

"Umbre!"

"Alright let's go" Tanner took off after Rachel with Umbreon in tow.

Tanner soon found himself sitting at a table in the park across the street from an Italian restaurant where Jason and Caroline were dining. Rachel sat across from him while Umbreon was siting on his shoulder.

"So, what are they doing now?" Rachel asked causing Tanner to sigh. He currently sat facing the restaurant meaning that Rachel's back was towards it. This meant she was often asking him to update her on what's going on.

The red capped trainer took a look towards the patio in front of the restaurant where Jason and Caroline sat. A waiter walked by and gave them their food. Caroline was the same age as Jason. She has orange hair, green eyes that are paler than Rachel's and a pair of thick rimmed glasses. Like Jason, she had exchanged her travel clothes, this time, for a formal looking dress.

"Uh, they've just gotten their food," Tanner craned his neck to get a better view.

"That's it?"

"Oh, now their laughing. I guess they were talking about you" Tanner said with smirk causing Rachel glare at him.

"Hey!" She exclaimed as she swatted Tanner's arm. That action caused Tanner to flinch which made Umbreon almost lose her balance.

"Ow" Tanner grumbled as he grabbed his bicep. Rachel snickered before she took a sip of the milkshake she had in front of her on the table. Umbreon glared at Rachel who, smirked.

As Tanner looked back towards Jason and Caroline, he couldn't help but wonder what it would be like to go on a date. Other than the mandatory dance for all of the participants of the Johto League, Tanner had never gone on a date. He went with Rachel to that dance but there was nothing romantic about that. Heck, he wasn't sure he could even call it a date. Rachel had volunteered to go with him because every girl he asked said no. He and Rachel are good friends, but they had a more brotherly and sisterly relationship.

Rachel was starting to lose her patience. Jason and Caroline haven't done or gone anywhere interesting. Worst of all, they sat in a spot where only Tanner could see them. It was annoying to have to ask Tanner for an update to make sure it didn't look like they're watching someone.

Both Rachel and Tanner were broken out of their thoughts by someone nearby speaking up.

"Well, if it isn't Tanner Riverton" Tanner turned to see his childhood rival, Wesley walking towards their table. Despite how bitter and childish they'd act towards each other in the past, Tanner and Wesley had both matured since then and now have a more mature, healthier rivalry.

"Hey Wesley" Tanner replied. "How many badges do you have?"

"Seven, you?" Wesley smirked confidently as he flicked his orangey brown hair to side.

"Dang it! I only have six!" Tanner groaned in frustration. Wesley was still ahead of him. He's got to regain ground fast.

"Hey Wesley" Rachel said as she stirred her milkshake with its straw. "What brings you to Lilycove City?"

"Oh, I met up with Laura in the safari zone and she wanted to check the department store, so I joined her" Wesley replied. "She's still there right now, I wanted to go get my Pokémon looked at by Nurse Joy."

"Oh cool, the department store is amazing!" Rachel beamed. "They have so many amazing TMs that contain a variety of beautiful moves. If only I had enough money to buy them all"

Tanner rolled his eyes at Rachel's obsession with Pokémon moves. Only when Rachel spoke about moves could he understand how she and Jason must feel when he speaks about battles.

"So, what brings you guys here? Wait, where's Jason? Are you guys on a date?" Wesley asked rapidly.

Tanner and Rachel both looked at him in shock with red on their faces.

"What! No! We would never!" Tanner yelled in shock as he stood up causing poor Umbreon to lose her balance again.

"Umbreon!" Umbreon complained to Tanner.

"EWWW!" Rachel yelled. "Yeah, do you really think I would date him!? Are you insane!?"

"Come on guys!" Wesley laughed. "I'm just messing with you guys. I know you two can barely stand each other as friends"

Tanner sighed as he relaxed and sat back down. Wesley always seems to know how to get under his skin.

"Now that we know you're not insane, I guess you can know why we're here, it also explains where Jason is." Rachel told Wesley who took immediate interest.

As Rachel was talking to Wesley, Tanner glanced towards the restaurant across the street. He noticed that Jason and Caroline were no where to be seen. Where could they have gone?

"So," Rachel started. "We came over here because I wanted to check out the department store, like Laura, but then Jason got a date! So now we're currently spying on-"

"Spying on who?"

Tanner and Rachel jumped when they saw Jason and Caroline standing next to their table. Wesley was struggling not laugh as Tanner and Rachel nervously chuckled. Umbreon rolled her eyes as, once again, her trainer's sudden movements almost made her fall off his shoulder. Umbreon hopped off of Tanner and onto the ground. She really has to stop siting on his shoulder, he makes too many sudden movements.

"Hey Jason, Caroline!" Tanner forced out trying to sound clueless. "What are you guys doing here? Aren't you two supposed be on a date?"

Rachel faced palmed at Tanner's attempt at saving her earlier blunder.

"Hi Tanner" Caroline smiled. Jason wrapped an arm around her shoulders before he spoke.

"Yeah, we had dinner at that restaurant over there" he said as pointed to the restaurant across the street. "When we were leaving we saw you two over here with Wesley and thought we'd say hi."

"Oh cool, Rachel and I decided we'd get some milkshakes and thought the park would be a great place to drink it. It's not like we were spying on y- ow" Tanner was cut of by Rachel elbowing him.

"On Wesley's date with Laura!" Rachel finished with a lie.

"What!?" Wesley exclaimed as his face turned red. He and Tanner looked at Rachel shocked.

"That's why you confronted us right?" Rachel gritted her teeth as she glared at Wesley. Wesley's turned white in fear at the look Rachel gave.

"Ha yeah…" Wesley chuckled nervously with a bright red blush on his face.

"Well it was nice to see you guys, but Caroline and I are going to see a play isn't that right?" Jason said somewhat passive aggressively.

"Yep! We're going to see Romeo and Juliet!" Caroline said. Her face made it unreadable to whether or not she had understood that Tanner and Rachel were spying on her date. The way Jason looked and spoke made it clear he figured it out.

"Let's get going then!" Jason said as he Caroline turned to leave. Tanner, Rachel and Wesley stayed quite while they walked away hand in hand. As the couple left, Jason turned and shot a gaze at Tanner and Rachel that made them both gulp.

"Well that happened." Tanner chuckled once Jason and Caroline left their sight. Wesley squirmed uncomfortably. Umbreon coed from the ground below Tanner, finally being able to rest without the treat of sudden movement. While Rachel leaned back into her chair.

The Pokémon move enthusiast was actually starting to feel better about the whole situation after Jason confronted them. Funny enough, despite how angry he may have looked, it was the same way Jason would react whenever she and Tanner team up against him. He might seem angry, but he'd always get over it quickly. She realized that no matter what happened, She, Tanner and Jason would always be great friends.

"Well, I'm gonna leave before Laura kills me or before Jason comes back" Wesley said, his face still red.

"Why? Do you actually have a date with Laura?" Tanner asked.

"What! No!" Wesley exclaimed as he turned to leave. "Don't you ever say anything to Laura about this!"

Tanner and Rachel burst into laughter as Wesley walked away. As their laughter died down, the two sat in silence as the sun started to set. Rachel seemed to be deep in thought.

"Something up?" Tanner asked Rachel, breaking the silence.

"No…. I was just thinking about what to do for the rest of the night" Rachel said quietly.

"Please don't tell me you still want to spy on Jason's date." Tanner pleaded as Umbreon hopped onto his lap, deciding the ground was too cold.

"Nah," Rachel giggled. "Romeo and Juliet is boring, not to mention that plays are for wusses"

Tanner let out a sigh of relief as Rachel said that. He didn't entirely want to spy on Jason and Caroline's date to begin with, he thought it was invasion of their privacy. Tanner decided to suggest something he thought both he Rachel would enjoy. The two of them had been bickering a lot more recently and being able to hang out without fighting while they spied on Jason was nice.

"Why don't we go and try to teach my Sceptile Grass Pledge again? We still got day light left, plus, I'm sure you'll get it this time!" Tanner suggested, trying to appeal to Rachel's interests.

"Sure," Rachel smiled as she stood up. "Sounds like fun!"

"Great!" Tanner grabbed Umbreon in his arms and also stood up.

Tanner carried Umbreon as he and Rachel walked back to the Pokémon centre. Rachel smiled as she walked back, feeling at peace with what was transpiring between Jason and Caroline. Despite her earlier fears, no matter what happened, relationships, different traveling companions, or whatever, Rachel now knows that she, Tanner and Jason would always be great friends, today was proof of that.

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 **Thanks for Reading!**

 **Remember** **to Find your path!**


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